Web Pentesting Beginner Roadmap (2026): From Recon to Server-Side Attacks

The Web Pentesting Beginner’s Roadmap: From Recon to Server-Side
A structured reference guide for anyone who just finished their first web security course.

After completing the Hacksmarter Web Pentesting course, I wanted to consolidate the methodology into a single source of truth. Whether you are preparing for a bug bounty or just securing your own apps, this is the mental framework you need.

1. Reconnaissance (The Foundation)

Pro-Tip: Always check robots.txt and sitemap.xml before running heavy scans. You’d be surprised what developers "hide" in plain sight.

Fingerprinting: Use Curl, Burp/Caido, or the Wappalyzer extension to identify the tech stack.

Directory Brute Forcing: Dirsearch, dirb, or gobuster to find hidden endpoints.

Subdomains & Vhosts: FFUF (with custom scripts) and gobuster.

Business Logic Prep: Become a user! Map out the site functionalities. What can a standard user do vs. an Admin?

OSINT: Google Dorks, Shodan, and Nmap for port scanning.

2. Authentication Assessment

Credential Attacks: Testing for weak passwords and credential stuffing.

MFA Bypass: Can you skip the 2FA step by manipulating the URL or response?

Password Resets: Testing for predictable tokens or Host Header Injection in reset links.

OAuth: Checking for misconfigured redirect URIs.

3. Session Management

Cookie Security: Ensure HttpOnly and Secure flags are set.

Session Fixation: Does the session ID stay the same after login? (It shouldn't).

JWT (JSON Web Tokens): Test for weak secrets or the infamous alg: none vulnerability.

4. Authorization (The "Permission" Gap)

IDOR (Insecure Direct Object Reference): Changing id=123 to id=124 to see someone else's data.

Broken Access Control: Accessing /admin as a guest.

Mass Assignment: Can you add "is_admin": true to a profile update JSON?

5. Client-Side Vulnerabilities

XSS: Reflected, Stored, and DOM-based attacks.

CSRF: Forcing users to perform actions without their consent (e.g., changing an email).

The Rest: Open Redirects, CORS misconfigurations, HTML Injection, and Clickjacking.

6. Server-Side Vulnerabilities

Injections: SQLi and NoSQLi.

SSRF: Forcing the server to make requests to internal metadata services (e.g., AWS/GCP).

File Uploads: Bypassing filters to upload a Web Shell (PHP/JSP).

Execution & Traversal: Path Traversal, SSTI (Template Injection), and OS Command Injection.